HU198902B - Process for production of derivatives of gamma-allenilgamma-amino butyric acid and medical compositions containing them - Google Patents
Process for production of derivatives of gamma-allenilgamma-amino butyric acid and medical compositions containing them Download PDFInfo
- Publication number
- HU198902B HU198902B HU842666A HU266684A HU198902B HU 198902 B HU198902 B HU 198902B HU 842666 A HU842666 A HU 842666A HU 266684 A HU266684 A HU 266684A HU 198902 B HU198902 B HU 198902B
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- HU
- Hungary
- Prior art keywords
- formula
- acid
- pharmaceutically acceptable
- acid addition
- acceptable acid
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 29
- 230000008569 process Effects 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title description 34
- 229940124277 aminobutyric acid Drugs 0.000 title description 2
- 239000002380 aminotransferase inhibitor Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 17
- -1 5- (1-methyl-1,2 -propadien-1-yl) -2-pyrrolide Chemical compound 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- XWILORJMRMFKPM-UHFFFAOYSA-N 4-aminohepta-5,6-dienoic acid Chemical compound C=C=CC(N)CCC(O)=O XWILORJMRMFKPM-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- IDKITPVRIHWVDP-UHFFFAOYSA-N 4-azaniumylocta-5,6-dienoate Chemical compound CC=C=CC(N)CCC(O)=O IDKITPVRIHWVDP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract description 15
- 229960003692 gamma aminobutyric acid Drugs 0.000 abstract description 9
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- 239000000284 extract Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004007 reversed phase HPLC Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 102100035923 4-aminobutyrate aminotransferase, mitochondrial Human genes 0.000 description 5
- 101710115046 4-aminobutyrate aminotransferase, mitochondrial Proteins 0.000 description 5
- 108090000340 Transaminases Proteins 0.000 description 5
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- 229910052786 argon Inorganic materials 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- 241000699670 Mus sp. Species 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Silicon Polymers (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51169183A | 1983-07-07 | 1983-07-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
HUT34435A HUT34435A (en) | 1985-03-28 |
HU198902B true HU198902B (en) | 1989-12-28 |
Family
ID=24036025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU842666A HU198902B (en) | 1983-07-07 | 1984-07-06 | Process for production of derivatives of gamma-allenilgamma-amino butyric acid and medical compositions containing them |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0134481B1 (es) |
JP (1) | JPS6036448A (es) |
KR (1) | KR850001151A (es) |
AT (1) | ATE31407T1 (es) |
AU (1) | AU566709B2 (es) |
CA (1) | CA1252477A (es) |
DE (1) | DE3468103D1 (es) |
DK (1) | DK335784A (es) |
ES (2) | ES8605468A1 (es) |
FI (1) | FI842723A (es) |
HU (1) | HU198902B (es) |
NO (1) | NO842759L (es) |
NZ (1) | NZ208805A (es) |
ZA (1) | ZA845237B (es) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5208345A (en) * | 1990-12-17 | 1993-05-04 | Merrell Dow Pharmaceuticals Inc. | Process for the production of (S)-vinyl and allenyl gaba |
IL100360A (en) * | 1990-12-17 | 1998-08-16 | Merrell Dow Pharma | HISTORY OF PYROLIDINONE USED AS SUBSTANCE (S) -Vinyl and Alanyl GABA |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960927A (en) * | 1975-03-18 | 1976-06-01 | Richardson-Merrell Inc. | Olefinic derivatives of amino acids |
US4178463A (en) * | 1978-01-30 | 1979-12-11 | Merrell Toraude Et Compagnie | Process for making 4-aminohex-5-enoic acid |
GB2120244B (en) * | 1982-05-17 | 1985-05-01 | Merrell Toraude & Co | Aminoalkadiene derivative |
-
1984
- 1984-07-06 AT AT84107917T patent/ATE31407T1/de not_active IP Right Cessation
- 1984-07-06 CA CA000458364A patent/CA1252477A/en not_active Expired
- 1984-07-06 ZA ZA845237A patent/ZA845237B/xx unknown
- 1984-07-06 NZ NZ208805A patent/NZ208805A/xx unknown
- 1984-07-06 NO NO842759A patent/NO842759L/no unknown
- 1984-07-06 AU AU30375/84A patent/AU566709B2/en not_active Ceased
- 1984-07-06 EP EP84107917A patent/EP0134481B1/en not_active Expired
- 1984-07-06 DK DK335784A patent/DK335784A/da not_active Application Discontinuation
- 1984-07-06 FI FI842723A patent/FI842723A/fi not_active Application Discontinuation
- 1984-07-06 JP JP59141292A patent/JPS6036448A/ja active Pending
- 1984-07-06 KR KR1019840003936A patent/KR850001151A/ko not_active Application Discontinuation
- 1984-07-06 HU HU842666A patent/HU198902B/hu not_active IP Right Cessation
- 1984-07-06 DE DE8484107917T patent/DE3468103D1/de not_active Expired
- 1984-07-06 ES ES534115A patent/ES8605468A1/es not_active Expired
-
1985
- 1985-07-16 ES ES545264A patent/ES8603169A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AU3037584A (en) | 1985-01-10 |
ES534115A0 (es) | 1986-04-01 |
CA1252477A (en) | 1989-04-11 |
FI842723A (fi) | 1985-01-08 |
DK335784D0 (da) | 1984-07-06 |
NZ208805A (en) | 1989-01-27 |
EP0134481B1 (en) | 1987-12-16 |
AU566709B2 (en) | 1987-10-29 |
ZA845237B (en) | 1986-02-26 |
ATE31407T1 (de) | 1988-01-15 |
NO842759L (no) | 1985-01-08 |
DK335784A (da) | 1985-01-08 |
ES545264A0 (es) | 1986-01-01 |
KR850001151A (ko) | 1985-03-16 |
HUT34435A (en) | 1985-03-28 |
FI842723A0 (fi) | 1984-07-06 |
EP0134481A1 (en) | 1985-03-20 |
JPS6036448A (ja) | 1985-02-25 |
DE3468103D1 (de) | 1988-01-28 |
ES8605468A1 (es) | 1986-04-01 |
ES8603169A1 (es) | 1986-01-01 |
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Legal Events
Date | Code | Title | Description |
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HU90 | Patent valid on 900628 | ||
HMM4 | Cancellation of final prot. due to non-payment of fee |